Rule No. 29: Leave the Jersey Better Than You Found It
Build what outlives your season
Hello, Dear Reader,
Welcome back to another week in The Playbook—Rules for Life. I pray this week is one where the warmth of familial ties holds you steady as you navigate through the rest of the holidays. I also pray that alongside physical gifts, you find the intangible ones tucked underneath the tree of your soul.
We’re three days away from Christmas. I tell you, where is the time racing away to? You’re probably in the mix of getting ready for Christmas Day, praying Amazon delivers your last-minute gifts (if you’re anything like me), and snuggled into the socks, sweaters, and blankets befitting the season. But before the big day, of course, there are the Christmas Eve parties, traditions, and the like, with hot toddies to boot as the temperatures continue to drop.
The girls and I (Suki and Lucy) are preparing for our first Christmas together. It’ll be Suki’s second with me, and if I’m lucky, she’ll let me put a hat on her.
A year ago, I wrote my first rule: Thoughts On Christmas Morning—8 Years of Christmas. It was the first entry in The Playbook. And as I sit here at my desk overlooking 90th Avenue, writing Rule 29, just one away from the finality of The Playbook, I can’t help but smile. I look back on the year that has passed: the highs, the lows, the moments when I cried my eyes out, feeling like my world was breaking, and the triumphs that came through steps taken to further my path on the road to creating a lasting legacy.
What a year it has been. A loved one of mine wrote on my birthday that she hoped 29 brought a year of wild growth, and I can say it has. It’s been uncomfortable, but as you know, I believe comfort is tested against the rubric of growth.
If this whole journey has taught me anything, it’s that we can build impressive things and still leave a room, and beyond that, a space, worse than we found it. We can “win” and still do damage to those around us and those coming next. We can be gifted and still make it harder for the next person to breathe, or even live.
So that’s where today’s rule lands:
RULE 29 – Leave the Jersey Better Than You Found It
Build Beyond You. Let Your Touch Outlive You.
The Lesson
What you carry is never just yours.
Anyone who has played sports, or worn a uniform in any capacity, knows it carries more than a name. It carries history, sacrifice, and the weight of those who wore it before you. What we sometimes forget is that it also carries the weight of responsibility, what you represent while you wear it.
I’ll never forget the first day I saw my name on the back of my high school basketball uniform: HAYNES above the number 14. A deep feeling of exuberance ran through me, followed by a deep sense of honor as my hands felt the texture of my school’s logo and emblem on the front. In that jersey, I was more than just D. Haynes. I was a reflection of The Bishops’ High School, its standard of excellence, and its culture formed long before I ever graced its halls.
That feeling was only magnified when I put my Guyana uniform on for the first time. There was Haynes on the back, the number 14 remained, and I became another person with the honor of representing his country.
I’m far removed from my days of playing basketball, but I think about the “jerseys” I wear when I’m out in the world and the logos that sit on the front. The Guyana flag, since I will always be a son of her soil. The St. John’s University crest, as a two-time alumnus. The windows of Turning Words Into Windows®, as I step into spaces as a CEO wearing many hats. And of course, the cross, as I step through the world saying I’m a Christian and a follower of Christ.
I’ve learned the “jersey” is never just yours. It belongs to something bigger than your current season. While we often see it as representation, it’s also a symbol of stewardship, saying I can be trusted with something. And as good stewards, we get our turn before we pass it on.
But leaving the jersey better doesn’t mean being perfect. It means being responsible, being integrous, and being concerned about what comes after you’ve put it down. It means that because you were here:
someone learned faster,
someone felt safer,
someone gained language for their experience,
someone found courage to try again,
someone inherited a healthier environment than you did.
But before you think about the future, you have to think about your present. The way you treat the jersey matters. It’s a reflection of how you treat yourself, the things you care about, and what you place value on. I remember the insistence of my coaches: never leaving mine haphazardly, dragging on the floor, or even wrinkled. In the same way, we must approach our legacy, because legacy is what remains after you leave the room, the spaces you occupy, and the communities your presence undoubtedly impacts.
In sports arenas, good veterans don’t just produce. They translate. They teach. They pass down the “small things” that aren’t small or insignificant: habits, discipline, timing, humility; how to lead when you’re not the star; how to respond when you lose; how to stay steady when you win. The same is true for life
Leaving the jersey better looks like:
mentoring without needing credit or recognition,
creating systems that don’t collapse when you’re absent,
protecting and enhancing culture instead of feeding chaos,
opening doors and leaving them open behind you,
refusing to make your insecurity someone else’s burden.
Because legacy isn’t what you accomplish. Legacy is what you hand off. And if we’re honest, some people don’t want to hand anything off. They want to be irreplaceable, but I’ve learned irreplaceability as a core motivation is often just unhealed ego dressed as importance.
Leaving a good legacy is also hard work. It means showing up on the days you don’t want to. Saying goodbye to people, spaces, and even opportunities that everything inside of you wants to cling to with every fiber of your being.
Legacy says: “I want you to win, do better, be better without needing you to need me.” It asks, “When the dust settles, what have I left standing that can endure the test of time?” It is planting trees you may never sit in the shade of.
The Reflection
Leave the way open behind you.
The truth is, I think about this rule a lot because I’ve lived both sides of it. I’ve been the person walking into spaces where the culture was already heavy, thick with toxicity. Where the standard was unclear, and the people in power were more committed to control than development. Where the community was fractured, and Ubuntu, I am because you are, was replaced with I am because you are nothing.
I’ve also been in spaces where someone left the jersey better, where the room felt safe enough for learning, failure, asking questions, and growth. Those spaces didn’t just produce results. They produced people.
That distinction deeply matters to me, especially as someone who came to New York from Guyana with very little except conviction, faith, and an internal promise to myself: If I ever build something, it has to help someone else stand, grow, and find the truth about themselves. I can admit I haven’t always gotten it right. My heart hasn’t always been in the right place, and I’ve crushed when my hands were only meant to hold. But that, too, is its own kind of learning.
I chuckle at how success is continually redefined for me. In Guyana, success was filtered through the lens of being the best athlete, being well-rounded, and being an asset to society. The last part remains. But when I moved to New York, success became: how much money am I making, what can I afford, and how does my image look?
I’m thankful I didn’t lean into that second definition, but it was certainly a challenge. It was hard to see everything I’ve been working toward, and everything I’ve achieved since I moved here, as success.
Increasingly throughout the years, especially the ones since I’ve begun teaching and leaning into my writing, I’ve seen the distinction between the kind of success that only climbs, and the other that builds stairs, a landing, and eventually a house for others to live in. I believe your ceiling should become someone else’s starting point. So I try to ask myself questions that keep me honest:
Am I leaving people clearer or more confused?
Am I leaving the room healthier or more tense?
Am I building capacity or creating dependence?
Am I elevating others or just protecting my role?
What is my motivation for doing this, self-promotion or purpose-driven?
What is the condition of my heart?
This rule is not sentimental for me. It’s spiritual, and it leans heavily on accountability. Because what we do in our season becomes the environment someone else will inhabit.
What the Word Says
In this season, I’ve realized how consistently Scripture frames life as stewardship, what we receive is not merely for consumption, but for cultivation and transfer.
“One generation shall praise Your works to another.” (Psalm 145:4)
Faith, testimony, and wisdom are meant to move through generations, not stop at our ego.“To whom much is given, much will be required.” (Luke 12:48)
Influence is not decoration. It is responsibility.“These words…you shall teach them diligently to your children.” (Deuteronomy 6:6–7)
Legacy is intentional. It is built through repetition, modeling, and presence. It’s also spiritual.“A good man leaves an inheritance to his children’s children, but the sinner’s wealth is laid up for the righteous.” (Proverbs 13:22)
“What you have learned and received and heard and seen in me, practice these things, and the God of peace will be with you.” (Philippians 4:9)
“What you have heard from me, entrust to faithful people who will be able to teach others also.” (2 Timothy 2:2)
“Each of you should use whatever gift you have received to serve others, as faithful stewards of God’s grace in its various forms.” (1 Peter 4:10)
In the last two, the pattern is explicit: first receive, then entrust, then multiply, and finally pass on.
The Practice
So, how do we actually live Rule 29 in a practical way, and not just poetically? Here are a few things to consider:
1) Audit what people inherit from you
Ask yourself: when people leave an interaction with me, what do they walk away with?
more clarity or more anxiety?
more courage or more shame?
more tools or more dependence?
You don’t need to be harsh, just honest. Honesty is the place where true reflection starts.
2) Build what can outlive your mood
Legacy requires structure.
Write things down.
Create repeatable systems.
Make the standard explicit.
Train people so the work doesn’t hinge on your constant presence.
A healthy culture is one that can function without the founder in the room.
3) Coach for multiplication, not attachment
If you lead, lead to replace yourself.
Teach someone the thing you do well.
Share your process, not just your results.
Give away what you wish someone gave you earlier.
You’re not losing power by teaching. You’re proving you have it.
4) Protect the next generation from your unresolved pain
This is the deepest layer of the rule.
If you don’t heal, you will hand your wounds to someone else as a “standard.” If you don’t confront your insecurity, you will build systems that punish others for being free.
Leaving the jersey better sometimes looks like doing your own internal work so you stop bleeding on the people coming after you.
5) Make it easier for someone to win this week
Not someday, this week. Especially as we remember the reason for the season.
Encourage a student with specificity.
Introduce two people who should know each other.
Share a resource you could have hoarded.
Give a younger version of you a clearer map.
Legacy is built in small acts that compound.
Rule No. 29
So here it is, plainly stated:
RULE 29 – Leave the Jersey Better Than You Found It
Build Beyond You. Let Your Touch Outlive You.
Leave language where someone needed light.
Even when your season ends, your stewardship still remains. It’s a reminder to me too. So my prayer is that God would mature your definition of success. Far beyond “Did I win?” to “Did I build?” Not just “Did I accomplish?” but “Did I leave something stronger?” Not just “Did they applaud?” but “Did someone else become braver and more authentic to themselves because I was here?”
Because the truest legacy is not just being remembered. It’s being responsible with what you were given so someone else can run faster, jump higher, soar further when it’s their turn to wear the jersey.
And even as you celebrate on Christmas morning, be reminded that we all have a chance at grace because of the legacy of Jesus Christ, who was born in a manger.
Merry Christmas to you, your family, and all your loved ones.
